Metronidazole → HCID 86758374, compound

HRID 2230069Notes

Reaction equation

HRID 2230069 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[CH3:16][C:17]1[N:21](CCO)[C:20]([N+:25]([O-:27])=[O:26])=[CH:19][N:18]=1>O>[CH3:16][C:17]1[NH:21][C:20]([N+:25]([O-:27])=[O:26])=[CH:19][N:18]=1.[N+:1]([C:4]1[O:8][C:7]([C:9]([O:11][CH2:16][CH3:17])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 4173MetronidazoleHCID 125775-Nitro-2-Furoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 86758374HCID 86758374, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The reaction mixture of 5-Nitro-2-furoic acid (157 mg, 1.0 mmol) and thionyl chloride (2 ml) was refluxed for 2 h. The excessive thionyl chloride was evaporated under vacuum. The residue was dissolved in 4 ml of dichloromethane. To this solution, metronidazole (152 mg, 0.89 mmol) was added. After the mixture was stirred at room temperature for 20 h, water was added to this mixture. The organic layer of dichloromethane was separated, washed with 5% Na2CO3, H2O, and brine, and then dried over MgSO4. The solvent was removed, and the residue was recrystallized from C2H5OH—EtOAc to give 36 mg 2-methyl-5-nitro-1H-imidazole-1-ethyl 5-nitro-2-furoate. m.p.: 150-152° C.

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe excessive thionyl chloride was evaporated under vacuum
  3. dissolutionThe residue was dissolved in 4 ml of dichloromethane
  4. customThe organic layer of dichloromethane was separated
  5. washwashed with 5% Na2CO3, H2O, and brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed
  8. customthe residue was recrystallized from C2H5OH—EtOAc

Sources & evidence

ORD record
ord-dd2f33099a6344e88ffadcec58a29188
Source dataset
uspto-grants-2002_07
Patent number
US06423707B1

Reaction notes

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